3,3′-Dimethyl-1,1′-ethyl­ene­diimidazolium dibromide

Chen, Y.; Song, W.; Xu, J.; Cui, R.; Tian, D.

doi:10.1107/S1600536809036009

Volume 65
Part 10
Page o2454
October 2009

Received 28 August 2009
Accepted 6 September 2009
Online 12 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
R = 0.059
wR = 0.160
Data-to-parameter ratio = 16.6
Details

3,3'-Dimethyl-1,1'-ethylenediimidazolium dibromide

Yu Chen,^a Wei Song,^a Juan Xu,^a Rui-bo Cui ^a and Dan-bi Tian ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: danbi@njut.edu.cn

The title compound, C₁₀H₁₆Br₂N₄, was synthesized by the reaction of 1-methylimidazole and 1,2-dibromoethane in toluene. The complete dication is generated by a crystallographic inversion centre situated at the mid-point of the ethane C-C bond. In the crystal structure, weak intermolecular C-HBr interactions link the molecules into chains along the b axis and an intramolecular C-HBr close contact is also present.

Related literature

For general background, see: Ding et al. (2007). For related literature, see: Peveling (2001); Takao & Kazuhiko (1997). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₁₆N₄²⁺·2Br^-
M_r = 352.07
Monoclinic, P 2₁ /c
a = 8.4750 (17) Å
b = 8.9620 (18) Å
c = 9.2390 (18) Å
= 107.73 (3)°
V = 668.4 (3) Å³
Z = 2
Mo K radiation
= 6.05 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.264, T_max = 0.583
1296 measured reflections
1212 independent reflections
862 reflections with I > 2(I)
R_int = 0.021
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.160
S = 1.01
1212 reflections
73 parameters
H-atom parameters constrained
_max = 0.80 e Å^-3
_min = -0.85 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2ABr	0.93	2.92	3.591 (8)	130
C1-H1BBrⁱ	0.96	2.97	3.738 (8)	138
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1985); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2872 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ding, Y. S., Zha, M., Zhang, J. & Wang, S. S. (2007). Colloids Surf. A: Physicochem. Eng. 298, 201-205.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft,The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Peveling, R. (2001). J. Orthopt. Res. 10, 171-187.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Takao, S. & Kazuhiko, M. (1997). Takasago International Corporation, Tokyo, Japan. EP Patent No. 0 755 937.

organic compounds